EP0143406A2 - Compositions liquides de colorants réactifs et leur utilisation - Google Patents

Compositions liquides de colorants réactifs et leur utilisation Download PDF

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Publication number
EP0143406A2
EP0143406A2 EP84113868A EP84113868A EP0143406A2 EP 0143406 A2 EP0143406 A2 EP 0143406A2 EP 84113868 A EP84113868 A EP 84113868A EP 84113868 A EP84113868 A EP 84113868A EP 0143406 A2 EP0143406 A2 EP 0143406A2
Authority
EP
European Patent Office
Prior art keywords
liquid
water
dye
weight
preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP84113868A
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German (de)
English (en)
Other versions
EP0143406B1 (fr
EP0143406A3 (en
Inventor
Konrad Dr. Opitz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
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Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0143406A2 publication Critical patent/EP0143406A2/fr
Publication of EP0143406A3 publication Critical patent/EP0143406A3/de
Application granted granted Critical
Publication of EP0143406B1 publication Critical patent/EP0143406B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0072Preparations with anionic dyes or reactive dyes
    • C09B67/0073Preparations of acid or reactive dyes in liquid form

Definitions

  • solubilizers or combinations of solubilizers with anionic dispersants described in the patent or laid-open specifications GB-PS 1 060 063, DE-OS 2 529 658 or DE-OS 31 26 081 for reactive dyes which are less readily soluble in water alone are used on C.I. Reactive Blue 19, although they are only described to achieve higher dyestuff contents in the liquid dye preparation or to improve the storage stability of such liquid dye preparations, there is also a slight improvement in the alkali resistance, which by no means meets the practical requirements. If the e-caprolactam mentioned in GB-PS 1 060 063 is used as a solubilizer, then in the case of warm storage there is also a marked loss of color strength.
  • liquid dyeing preparations of reactive dyes including C.I. Reactive Blue 19, known, which are characterized by the addition of nonionic dispersants from the group of the ⁇ -methylbenzyl group-containing oxalkylates of aromatic hydroxy compounds.
  • These additives improve the shelf life, especially in view of the undesirable increase in viscosity when stored at low temperatures.
  • they do not solve the problem of the alkali resistance of C.I. Block and dyeing liquors containing Reactive Blue 19.
  • the present invention now relates to C: I.
  • the liquid dyeing preparations according to the invention, as well as padding and dyeing liquors produced therewith or wastewater resulting therefrom do not tend to foam.
  • the liquid dyeing preparations according to the invention are characterized by a content of 10 to 50% by weight of CI Reactive Blue 19, 5 to 50% by weight of one or more anionic dispersants from the group of the lignosulfonates or from the group of the condensation products of formaldehyde with naphthalenesulfonic acid or with a naphthalenesulfonic acid substituted with 1 to 3 lower alkyl groups, 1 to 30% by weight of the sodium salt of the anthraquinone -2-sulfonic acid,
  • liquid dyeing preparations according to the invention can also contain preservatives against fungal and bacterial attack.
  • Anthraquinone-2-sulfonic acid sodium is described in DE-PS 2 412 964 as one of several additional components of a powdered preparation of CI Reactive Blue 19 with advantageous properties in block and exhaust dyeings. Due to the extremely low water solubility of anthraquinone-2-sulfonic acid sodium (0.43% at 20 ° C, see Beilstein, vol. 11, second supplementary work, p. 194), which was known from the literature, it was not to be expected that the improvement in Alkali resistance of padding and dyeing liquors required the amount of anthraquinone-2-sulfonic acid sodium to be dissolved in the most concentrated liquid dyeing preparations possible.
  • the liquid dyeing preparations according to the invention contain significantly more anthraquinone-2-sulfonic acid sodium than the water solubility of this compound corresponds (1% anthraquinone-2-sulfonic acid sodium in a liquid dyeing preparation containing 83% water, corresponds to a content of 1.19% in anthraquinone-2 -sulfonic acid sodium in the in the liquid Color preparation contains the amount of water, which is almost three times the solubility of the anthraquinone-2-sulfonic acid sodium in pure water (for the other claimed compositions of the liquid preparations is the concentration of anthraquinone-2-sulfonic acid sodium, based on the amount of water contained therein, even higher)), this does not result in any of the disadvantages to be expected, such as precipitation during storage, in particular also not during storage for longer periods of several weeks or at low temperatures below 5 ° C.
  • Particularly preferred liquid dyeing preparations contain 15-30% by weight of C.I. Reactive Blue 19, 5-30 wt .-% of a condensation product of formaldehyde and naphthalenesulfonic acid, which can be substituted with lower alkyl groups, 2- 20 wt .-% sodium salt of anthraquinone-2-sulfonic acid, 1-5 wt .-% of one or several buffer substances and 40-77 wt .-% water.
  • the liquid dyeing preparations according to the invention are prepared by dissolving C.I. Reactive Blue 19 in water with the addition of one or more anionic dispersants and with the addition of anthraquinone-2-sulfonic acid sodium.
  • the production takes place in such a way that C.I. Reactive Blue 19 in dry or moist form, for example as a moist filter cake, at room temperature or up to 50 ° C elevated temperature together with one or more anionic dispersants and anthraquinone-2-sulfonic acid sodium is dissolved with stirring.
  • Another manufacturing option is a or to add several anionic dispersants and anthraquinone-2-sulfonic acid sodium to the dye solution present at the end of the dye synthesis and, if necessary, to either distill off part of the water under reduced pressure or additionally solid CI Reactive Blue 19, which is obtained by drying part of the water, to achieve a higher dye content the solution obtained was obtained, entered and dissolved.
  • the liquid dye formulations of C.I: Reactive Blue 19 according to the invention are particularly stable in storage and do not lead to any precipitation, even after storage for several weeks, either at room temperature or at temperatures raised to 50 ° C. or at a temperature of 0 ° C. In addition, the reactivity of the dye remains unaffected, so that there is no loss of color strength. In addition, neither the liquid dyeing preparations according to the invention nor the padding or dyeing liquors produced therewith nor the resulting wastewater tend to foam.
  • the preparations according to the invention for dyeing and printing natural, such as wool and silk, and synthetic polyamide fiber materials or fiber materials made from natural or regenerated cellulose, such as cotton, linen, cellulose and viscose silk, and fiber mixtures are one or more of the named Contain types of fibers, particularly suitable.
  • the dyeing preparations according to the invention are particularly suitable for the preparation of padding and dyeing liquors with excellent alkali resistance.
  • liquid dye preparation containing 13.75% by weight of pure dye and having a pH of 4.4 are obtained, with 25% of the color strength of a powdered commercial product from C.I. containing 55% by weight of pure dye.
  • Reactive Blue 19 This liquid color preparation is characterized by very good storage stability at low or elevated temperatures, e.g. when stored at 50 ° C for six weeks or at 0 ° C for one week without dye or other deposits occurring. The color strength remains unchanged when stored under the conditions mentioned. This also applies to fluidity. Pad or dyeing liquors produced using this liquid dyeing preparation have very good alkali resistance and are just as little inclined to foam as the liquid dyeing preparation itself.
  • CI Reactive Blue 19 sodium salt
  • 294 parts of Water dissolved After heating to 50 ° C., 10 parts of anthraquinone-2-sulfonic acid sodium, 25 parts of naphthalenesulfonic acid-formaldehyde condensation product, 4 parts of sodium borate and 2 parts of oxalic acid are introduced and dissolved. After clarification with the addition of 5 parts of filter aid, 400 parts of a liquid dyeing preparation with a pH of 6 are obtained, which have the same advantageous properties as described in Example 1.
  • Example 1 If the procedure is as described in Example 1, but using 5 parts of anthraquinone-2-sulfonic acid sodium and 30 parts of naphthalenesulfonic acid-formaldehyde condensation product and concentration under reduced pressure to also 400 parts, a liquid dyeing preparation with the same advantageous properties is obtained, as described in Example 1.
  • Example 1 If the naphthalenesulfonic acid-formaldehyde condensation product in Example 1 is replaced by a dimethylnaphthalenesulfonic acid-formaldehyde condensation product and the procedure is otherwise as described there, a liquid dyeing preparation having the same advantageous properties as described in Example 1 is obtained.
  • 600 parts of a dye solution obtained in the production of CI Reative Blue 19 using a known method and having a solids content of 10.5% by weight or 9.2% by weight of pure dye are stirred at 30-55 ° C. with 30 parts of naphthalenesulfonic acid formaldehyde -Condensation product, 5 parts of anthraquinone-2-sulfonic acid sodium, 4 parts of sodium acetate and 2 parts of acetic acid were added and the mixture was stirred for a further 30 minutes. 239 parts of water are then distilled off under reduced pressure in a rotary evaporator.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
EP84113868A 1983-11-24 1984-11-16 Compositions liquides de colorants réactifs et leur utilisation Expired - Lifetime EP0143406B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3342432 1983-11-24
DE19833342432 DE3342432A1 (de) 1983-11-24 1983-11-24 Fluessige reaktivfarbstoffzubereitungen und ihre verwendung

Publications (3)

Publication Number Publication Date
EP0143406A2 true EP0143406A2 (fr) 1985-06-05
EP0143406A3 EP0143406A3 (en) 1987-10-14
EP0143406B1 EP0143406B1 (fr) 1990-03-14

Family

ID=6215111

Family Applications (1)

Application Number Title Priority Date Filing Date
EP84113868A Expired - Lifetime EP0143406B1 (fr) 1983-11-24 1984-11-16 Compositions liquides de colorants réactifs et leur utilisation

Country Status (7)

Country Link
US (1) US4589885A (fr)
EP (1) EP0143406B1 (fr)
JP (1) JPS60134078A (fr)
KR (1) KR930002549B1 (fr)
BR (1) BR8405962A (fr)
DE (2) DE3342432A1 (fr)
IN (1) IN163701B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0318023A3 (fr) * 1987-11-27 1991-06-19 Hoechst Japan Limited Colorants réactifs
WO1992006140A1 (fr) * 1990-09-27 1992-04-16 Hoechst Aktiengesellschaft Procede de preparation de solutions aqueuses concentrees de colorants azoiques anioniques

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0676561B2 (ja) * 1985-07-16 1994-09-28 住友化学工業株式会社 反応染料の液状水性組成物
ES2067458T3 (es) * 1987-07-22 1995-04-01 Mitsubishi Chem Ind Mezcla colorante soluble en agua y metodo de coloracion.
DE3842054A1 (de) * 1988-12-14 1990-06-21 Bayer Ag Farbstoffpraeparationen
US5116396A (en) * 1989-05-12 1992-05-26 Union Carbide Industrial Gases Technology Corporation Hybrid prepurifier for cryogenic air separation plants
US5968241A (en) * 1997-02-14 1999-10-19 Binney & Smith Inc. Washable coloring composition
US5981626A (en) * 1997-02-14 1999-11-09 Binney & Smith Inc. Washable coloring composition suitable for use in dry erase markers
US5900094A (en) * 1997-02-14 1999-05-04 Binney & Smith Inc. Image transfer method for use with water based dry erase markers
AUPP570898A0 (en) * 1998-09-07 1998-10-01 Rocklea Spinning Mills Pty. Limited Method of dyeing cotton/wool blends
CN1329456C (zh) * 2004-10-15 2007-08-01 东港工贸集团有限公司 一种活性染料耐碱稳定剂
CN102321392B (zh) * 2011-06-09 2015-07-15 天津德凯化工股份有限公司 一种耐碱性蓝色活性染料及其制备方法
CN102260419B (zh) * 2011-06-09 2015-07-15 天津德凯化工股份有限公司 一种耐碱性的染料组合物
CN102260418B (zh) * 2011-06-09 2015-07-15 天津德凯化工股份有限公司 一种耐碱性蓝色活性染料组合物
CN102321393B (zh) * 2011-06-09 2015-07-15 天津德凯化工股份有限公司 一种耐碱性活性染料组合物
CN102250493B (zh) * 2011-06-09 2015-07-15 天津德凯化工股份有限公司 一种耐碱性蓝色活性染料
JP6238685B2 (ja) * 2013-11-08 2017-11-29 日本化薬株式会社 水性分散液、インク組成物及びインクジェット捺染方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN140836B (fr) * 1974-03-18 1976-12-25 Hoechst Ag
US4149850A (en) * 1974-04-09 1979-04-17 Hoechst Aktiengesellschaft Liquid preparations of reactive dyestuffs
IN143734B (fr) * 1974-04-09 1978-01-21 Hoechst Ag
AR207270A1 (es) * 1974-11-20 1976-09-22 Hoechst Ag Preparaciones liquidas acuosas de colorantes procedentes de colorantes reactivos que son 1-(4"-sulfofenil)-3-metil-5-pirazol-5-ona-4-il-azo-(2'-metoxi-5'metil-(4"-sulfofenil)-3-metil-5-pira-4'-(beta-sulfatoetil))-benceno y 1-zol-5-ona-4-il-azo-(2',5'-dimetoxi-4'-(beta-sulfatoetil))-bencen
US4283195A (en) * 1979-02-13 1981-08-11 Sumitomo Chemical Company, Limited Dyestuff composition for dyeing or printing cellulose fiber materials
JPS5673181A (en) * 1979-11-13 1981-06-17 Sumitomo Chemical Co Reactive dyestuff composition for cellulose fiber
JPS6054438B2 (ja) * 1980-03-31 1985-11-29 住友化学工業株式会社 セルロ−ス系繊維材料の染色用反応染料液状組成物
DE3104605A1 (de) * 1981-02-10 1982-08-19 Hoechst Ag, 6000 Frankfurt Farbstoffzubereitungen und ihre verwendung
DE3126081A1 (de) * 1981-07-02 1983-01-20 Hoechst Ag, 6000 Frankfurt Fluessige reaktivfarbstoffzubereitungen und ihre verwendung
JPS58142941A (ja) * 1982-02-19 1983-08-25 Sumitomo Chem Co Ltd セルロ−ス繊維用反応染料組成物

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0318023A3 (fr) * 1987-11-27 1991-06-19 Hoechst Japan Limited Colorants réactifs
WO1992006140A1 (fr) * 1990-09-27 1992-04-16 Hoechst Aktiengesellschaft Procede de preparation de solutions aqueuses concentrees de colorants azoiques anioniques
TR26431A (tr) * 1990-09-27 1995-03-15 Hoechst Ag ANIYONIK AZO BOYAR MADDELERININ KONSANTRE, SULU CÖZELTILERININ üRETILMESINE MAHSUS USUL.
US5508389A (en) * 1990-09-27 1996-04-16 Hoechst Aktiengesellschaft Process for producing concentrated aqueous solutions of anionic azo dyes

Also Published As

Publication number Publication date
EP0143406B1 (fr) 1990-03-14
IN163701B (fr) 1988-10-29
US4589885A (en) 1986-05-20
DE3342432A1 (de) 1985-06-05
DE3481624D1 (de) 1990-04-19
JPS60134078A (ja) 1985-07-17
JPH0579705B2 (fr) 1993-11-04
EP0143406A3 (en) 1987-10-14
KR930002549B1 (ko) 1993-04-03
BR8405962A (pt) 1985-09-10
KR850003558A (ko) 1985-06-20

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